Sodium Carbonate → HCID 86671496, 화합물

HRID 536627

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HRID 536627 반응식
Br[C:2]1[C:6]([Br:7])=[CH:5][S:4][C:3]=1[CH:8]=[O:9].[CH3:10][C:11]1[CH:12]=[C:13]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:14]=[CH:15][C:16]=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O>[Br:7][C:6]1[C:2]([C:16]2[CH:15]=[CH:14][C:13]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])=[CH:12][C:11]=2[CH3:10])=[C:3]([CH:8]=[O:9])[S:4][CH:5]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 125595283,4-Dibromothiophene-2-carbaldehydeHCID 66715578HCID 66715578, 화합물

생성물 1

HCID 86671496HCID 86671496, 화합물수율 323.9%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
100 °C

실험 절차

To the solution of Intermediate 1 (4 g, 15 mmol) in a mixture of DME and H2O (150 mL/50 mL) were added N-(3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (3.6 g, 1.65 mmol) and Na2CO3 (2.8 g, 3.1 mmol), the mixture was degassed with N2, and Pd(PPh3)4 (500 mg) was added, then the mixture was heated to 100° C. under N2 overnight. The reaction solution was concentrated to remove the organic solution, then the aqueous layer was extracted with EtOAc (100 mL×3). The combined organic layers were washed with brine, dried over Na2SO4, concentrated under reduced pressure, the residue was purified by column chromatography to give N-(4-(4-bromo-2-formylthiophen-3-yl)-3-methylphenyl)methanesulfonamide (2.0 g, yield 35.7%).

후처리

  1. customthe mixture was degassed with N2, and Pd(PPh3)4 (500 mg)
  2. additionwas added
  3. concentrationThe reaction solution was concentrated
  4. customto remove the organic solution
  5. extractionthe aqueous layer was extracted with EtOAc (100 mL×3)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-1494e7372e5247a1b3caa74ff144e352
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859611B2

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